I’ve been lucky to have a few meaningful, high-quality conversations lately.
Talks that have left me brimming with energy and ideas. Discussions where I could have gone on talking for hours if I didn't have to head to the next appointment. Conversations where the topics and ideas bounced off each other like balloons filled with helium.
At the same time, there are conversations that fall short of this standard. Small talk at corporate functions, strained hellos at cocktail parties, chatting about the economy at the barbeque. These interactions rob you of energy and have you looking for the nearest Exit sign. The balloons pop and fall to the ground.
We spend a large chunk of our day in conversation. It's clear that better conversations can improve the quality of our ideas and our lives. Can we parametrize this ‘thing’ we do every day that’s ‘mushy’ and intangible, but has high value if done right?
What are the elements of a “good” conversation? And, having defined this, can we foster more of these conversations?
It all started with an overpriced coffee
Online writer and entrepreneur, Adam Tank, came to Munich a couple of months ago. We hadn’t met in person before, but we knew each other from our writing community.
We had a short window early on a Friday morning before he had to fly back to the States. I could easily have slept in or gone for a run instead. He could’ve done the same. But we decided to make it happen.
It turned out to be a great chat. Well worth the seven Euros per Americano. We spoke about topics that got us both buzzing… writing online, time spent in South Africa, the pros and cons of doing an MBA. We also opened up about our backgrounds and future ambitions… I want to make a go of being a creator. Adam as well, but for now he’s focused on his water-tech startup.
We scheduled 45 minutes, but ended up talking for an hour and a half. He almost missed his flight.
Afterwards, we tried to formulate why this particular conversation was so fun and if there were some common features to generative, high-energy conversations.
The perfect brew
"Sometimes you just know someone is an OG", like Adam says. There is a good vibe. You ‘click’. It’s more than first impressions. It’s something ethereal.
Other times there's less chemistry. The conversation lags. There are some silences. You can feel your brain scratching around in the chicken coop for a common thread.
I'm curious - are there ways to 'save' the conversations where things aren't flowing? And can we apply these elements to improve the quality of all conversations, even when they are going well?
Like when you're brewing a cup of coffee. The use of high-quality beans invariably leads to a great taste and aroma. But there are other elements that also contribute to the perfect brew, including water temperature, brewing method and cleanliness to name a few. What are these elements for conversation?
Here are three things that make my interactions better:
- Being present: are there zero distractions?
- Finding shared interests: how much do your circles intersect?
- Opening up: are you prepared to be vulnerable?
I know this list isn't exhaustive and your own list may vary. It’s an attempt at defining the elements of a good interaction so we can become conversation enablers. We can become the baristas that know how to create a good brew even when the beans are not first-rate.
1. Being present
It all starts with paying attention to the other person.
By letting go of distractions, you show the other person that you respect their time. You make them feel seen. You signal that there is nothing better you would rather be doing in that moment.
Angel investor Naval Ravikant had this to say about being interviewed by Joe Rogan:
The good news is we can work on this skill. We can become better conversationalists. We can become like Joe.
During our conversation, Adam didn’t look at his phone once. He was completely present. This laid the foundation for a great interaction. We could just talk and spitball ideas without any external interruptions.
Sidebar: Adam runs a TikTok channel (the Pretend Extrovert) with 50,000+ subs on nurturing better social interactions, so he might have heard about the no-phones-on-the-table rule before.
Be a mirror:
Give your conversation partner space to form his or her ideas without interruption. Act like a mirror by picking up what excites them and reflecting what they say back to them as a question. This will make them feel heard.
Writer and coach, Rik van den Berge, is a great listener. Whenever I speak to him, I get the feeling that he ‘gets’ me. He never interrupts me or cuts me short. He lets me get into flow. If I stumble, he lets me hang. He doesn’t offer help or end my sentences for me. In this way I don’t get an easy out. As he says, “you already know the answer, you just need to put it into words.”
Be this person for your conversation partner.
Take a step back:
During your conversation, step back and observe the conversation from a higher level. Swim out onto the bank of the river instead of being pulled into the flow of it.
In this way, you can steer the conversation to a higher level.
You can also observe your own thoughts and feelings instead of identifying with them. Ask yourself – am I closing off or opening up? Do I feel defensive or expansive?
Meditation is one way of practising the act of stepping onto the river bank. Not only will it help you in your interactions with others, it will also raise the level of your internal conversations and self-talk.
2. Finding shared interests
Apart from being present, establishing shared interests sets a great foundation for a good conversation.
If your interests represent one circle and those of your conversation partner represent another, how much do your circles intersect?
If there is a large enough overlap, as was the case for Adam and I, odds are you will find a connection given enough time to explore each others’ interests.
In cases where your circles don't intersect that well, you can still find common ground.
You can’t force shared interests, but it always helps to be curious.
I like talking about online writing, Sam Harris’s podcasts, Paul Graham’s essays, Booker prize winning novels, hiking trails, running (a lot of running), the Springboks and even work sometimes. It’s a mixed bag.
This might not be everyone’s cup of tea. Maybe you’re more into gaming. Or knitting. Or Magic cards. Or book clubs. The list goes on.
We can still be friends. By showing interest and asking good questions, we can build a connection.
This is also one of the main qualities writer Charlie Bleecker looks for in a conversation partner:
“Another thing to look for is someone who asks good questions. Someone who is curious and engages and really listens to your response. This one seems obvious but lots of people actually suck at this.” via Transparent Tuesdays
You can learn something from everyone.
Everyone has an interesting story to share, no matter their class or their background or where they come from. If you can overcome your pretensions and biases, you can zone in on their story. And, who knows, maybe you’ll be wiser for it.
By being curious you show respect and a good attitude.
Surround yourself with interesting people:
You can also be more proactive. You can take steps to increase the likelihood of high-energy conversations coming your way.
By surrounding yourself with people that are curious and generative and score high on openness, you naturally participate in better discussions.
I like George Mack’s recommendation to seek out decentralised friend groups:
Centralised friend groups - You have one large cluster of friends. They all
have a lot in common and share the same history, beliefs and behaviours.
They usually fit in one box: "School friends" or "Work friends".
Decentralised friend groups - You have many small clusters of different friends who aren't connected. The only thing they have in common is that
they know you. Ambitious friends, fun friends, serious friends, relaxed friends, fitness friends, hometown friends, travelling friends etc - via How to think for yourself.
This has been the case for me over the last year. Starting my online writing journey has opened up many new doors. One of the stand-out benefits has been the interaction with highly talented, curious people from diverse backgrounds. I have caught myself saying “I really like this conversation” more frequently.
Think about which societies or groups you can plug into to expand your range. Try to find the most interesting people in your city. Better yet, start a podcast and interview the people you would love to speak to. That's a win-win for everyone.
3. Opening up (vulnerability)
This is a big one.
You are mindful. You have found shared topics. But are you prepared to open up? Do you have the strength to be vulnerable and know that whatever happens, you will be OK afterwards?
By opening up, you will have richer, more meaningful interactions. The most growth happens here. You will learn more about others and yourself in the process.
Ask deeper questions:
If you see that your partner wants to open up, you can egg them on by asking deeper questions.
I like Derek Sivers's approach to breaking the ice and connecting with people:
"When talking with people, ask deep open-ended questions — like “What’s your biggest regret?” — that will lead to unexpected stories."
Kelly Kraft shared a similar rule (the Rule of 3) in 68 bits of unsolicited advice:
“Rule of 3 in conversation. To get to the real reason, ask a person to go deeper than what they just said. Then again, and once more. The third time’s answer is close to the truth.”
Being vulnerable takes guts, but it shows that we’re human. It shows that we’re all in this thing together.
I need to run
It’s time to say goodbye. Adios.
Thanks for reading, which in itself is a special form of conversation.
I’ll leave you with this –
Sometimes you instantly get along with your conversation partner. Other times, your thought balloons are at risk of bursting and sagging to the ground. The good news is there are elements of conversation you can control. By being present, finding shared interests and opening up, you can still brew up a good conversation even when you don't have the best beans.
Thanks to Rik van den Berge for reading drafts of this essay and Adam Tank for the conversation that inspired it.
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